Photocatalytic Umpolung Synthesis of Nucleophilic π-Allylcobalt Complexes for Allylation of Aldehydes

被引:31
|
作者
Shi, Caizhe [1 ]
Li, Fusheng [1 ]
Chen, Yuqing [1 ]
Lin, Shuangjie [1 ]
Hao, Erjun [2 ]
Guo, Zhuowen [1 ]
Wosqa, Urwa Tul [1 ]
Zhang, Dandan [1 ]
Shi, Lei [1 ,2 ]
机构
[1] Dalian Univ Technol, Zhang Dayu Sch Chem, State Key Lab Fine Chem, Dalian 116024, Liaoning, Peoples R China
[2] Henan Normal Univ, Henan Key Lab Organ Funct Mol & Drug Innovat, Key Lab Green Chem Media & React, Minist Educ,Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China
来源
ACS CATALYSIS | 2021年 / 11卷 / 05期
关键词
pi-allylcobalt complexes; photoredox catalysis; allylation; umpolung; alcohol;
D O I
10.1021/acscatal.0c05330
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The concept of "umpolung" reactivity of p-allylmetal complexes has been developed as a powerful method for the allylation of aldehydes. This paper describes the photocatalytic umpolung strategy for the synthesis of nucleophilic allylcobalt complexes through a single-electron-transfer (SET) process. This strategy enables the metallaphotoredox allylation of carbonyls with allyl acetate using organic N,N-diisopropylethylamine as the terminal reductant bypassing the use of a stoichiometric amount of metals. Ultraviolet-visible spectroscopy was used to monitor the redox changes of cobalt in the reaction.
引用
收藏
页码:2992 / 2998
页数:7
相关论文
共 50 条
  • [41] Recent advances in the photocatalytic synthesis of aldehydes
    Wang, Yi
    Liu, Xiao-Fei
    He, Wei-Min
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (16) : 4198 - 4210
  • [42] Photocatalytic Barbier reaction-visible-light induced allylation and benzylation of aldehydes and ketones
    Berger A.L.
    Donabauer K.
    König B.
    König, Burkhard (Burkhard.Koenig@chemie.uni-regensburg.de), 2018, Royal Society of Chemistry (09) : 7230 - 7235
  • [43] Photocatalytic Barbier reaction - visible-light induced allylation and benzylation of aldehydes and ketones
    Berger, Anna Lucia
    Donabauer, Karsten
    Koenig, Burkhard
    CHEMICAL SCIENCE, 2018, 9 (36) : 7230 - 7235
  • [44] Synthesis of α-Quaternary Formimides and Aldehydes through Umpolung Asymmetric Copper Catalysis with Isocyanides
    Ohmiya, Hirohisa (ohmiya@sci.hokudai.ac.jp), 1600, American Chemical Society (139):
  • [45] Catalytic asymmetric allylation of aldehydes using the chiral (salen)chromium(III) complexes
    Kwiatkowski, Piotr
    Chaladaj, Wojciech
    Jurczak, Janusz
    TETRAHEDRON, 2006, 62 (21) : 5116 - 5125
  • [46] Enantioselective allylation of aldehydes catalyzed by new bifunctional bisoxazoline-metal complexes
    Takeuchi, Keiichi
    Takeda, Takuma
    Fujimoto, Tetsuya
    Yamamoto, Iwao
    TETRAHEDRON, 2007, 63 (24) : 5319 - 5322
  • [47] Synthesis of α-Quaternary Formimides and Aldehydes through Umpolung Asymmetric Copper Catalysis with Isocyanides
    Hojoh, Kentaro
    Ohmiya, Hirohisa
    Sawamura, Masaya
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (06) : 2184 - 2187
  • [48] Synthesis of Homoallyl Ethers via Allylation of Acetals and Aldehydes in Ionic Liquids
    Mohan, Ram S.
    Anzalone, Peter W.
    IONIC LIQUIDS IN ORGANIC SYNTHESIS, 2007, 950 : 104 - 115
  • [49] Strained silacycles in organic synthesis: A new reagent for the enantioselective allylation of aldehydes
    Kinnaird, James W. A.
    Ng, Pui Yee
    Kubota, Katsumi
    Wang, Xiaolun
    Leighton, James L.
    Journal of the American Chemical Society, 2002, 124 (27): : 7920 - 7921
  • [50] Strained silacycles in organic synthesis: A new reagent for the enantioselective allylation of aldehydes
    Kinnaird, JWA
    Ng, PY
    Kubota, K
    Wang, XL
    Leighton, JL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) : 7920 - 7921